Chloroacetyl chloride → n'-(2-Chloroacetyl)benzohydrazide

HRID 2119360Notes

Reaction equation

HRID 2119360 reaction equation
[C:1]([NH:9][NH2:10])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:11][CH2:12][C:13](Cl)=[O:14].ClCC(NN)=O>C1(C(C2C=CC=CC=2)CCN2CCCNCC2)C=CC=CC=1.CO.C(Cl)Cl>[C:1]([NH:9][NH:10][C:13](=[O:14])[CH2:12][Cl:11])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 11955BenzoylhydrazineHCID 101883Chloroacetyl hydrazine

Product 1

HCID 736972n'-(2-Chloroacetyl)benzohydrazideYield 54.5%

Reagents, catalysts & solvents 2

HCID 234410351-(3,3-Diphenyipropyl)homopiperazineCatalystHCID 21226129Dichloromethane methanolSolvent

Procedure

1-Benzoyl-2-(chloroacetyl)hydrazine (850 mg, 54%) was prepared from benzhydrazide (1.00 g, 7.34 mmol) and chloroacetyl chloride (0.58 mL, 7.34 mmol, 1 equiv) using general procedure. Compound No. 78 (300 mg, 51%) was prepared from 1-(3,3-diphenyipropyl)homopiperazine (100 mg, 0.34 mmol) and 1-benzoyl-2-(chloroacetylhydrazine (80 mg, 0.38 mmol) employing general alkylation procedure. TLC Rf=0.44 (10% CH3OH—CH2Cl2), RPLC tR=5.85 min (>85%), 220 nm (Method B): ESI/MS m/e 471.3 (M++H, C29H34N4O2).

Sources & evidence

ORD record
ord-90d9aee2f108471986c00eea03921ef5
Source dataset
uspto-grants-2004_02
Patent number
US06686353B1

Reaction notes

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